Significance: A novel electron-deficient poly(pphenylene vinylene) (PPV) is synthesized using dicarboxylic imide moieties as the electron-withdrawing groups. They were found to have good thermal stability, a high electron affinity (3.60 eV), and significant ordering in the solid state via p-p interactions. These polymers show promise for use in n-channel FETs and all-polymer-based solar cells.Comment: The use of the Diels-Alder reaction followed by oxidation is an interesting pathway to the phthalimide monomer. The choice of a Horner-Wadsworth-Emmons olefination for polymerization over a more traditional Gilch polymerization (which theoretically can be accomplished from the dibromo monomer) is also interesting. The yields of all reactions are moderate to good (35-90%). OTBDMS TBDMSO O O O TBDMSO TBDMSO N O O TBDMSO TBDMSO N O O HO HO N O O Br Br N O O O O N O O (EtO) 2 P (EtO) 2 P N O O R R R R R R or dove-tailed amine sulfur PBr 3 , Et 2 O 0 °C to r.t. P(OEt) 3, reflux PCC, CH 2 Cl 2 , r.t. maleic anhydride O O n + R = C 12 H 25

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

No abstract